Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 12, Problem 12.18P
Interpretation Introduction

Interpretation:

The reactant which can be epoxidized using MCPBA to get the given compound is to be determined.

Concept introduction:

MCPBA contains a peroxycarboxylic acid (-COOOH) group, which acts as an electrophile. The oxygen atom from this group simultaneously forms bonds to both carbon atoms of the alkene double bond to form an epoxide (oxirane) ring. The π electron pair from the double bond forms one bond, while one of the lone pairs of the oxygen atom forms the other bond. The result is a replacement of the π bond with two σ bonds.

The cis-trans stereochemistry about the carbon-carbon double bond is retained in the reaction.

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Organic Chemistry: Principles and Mechanisms (Second Edition)

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